Ben Erez is a former founder and product leader turned solopreneur and instructor. He teaches a popular Maven course for aspiring product managers, hosts the podcast Supra Insider, and is a proud girl dad living in Brooklyn.

In this episode, Ben shares what it’s like raising a daughter while building a portfolio career on his own terms. We discussed:

• How solo parenting can feel easier: Why Ben finds weekday solo parenting less stressful than co-parenting, and how clarity in routine helps him stay grounded.
• Making the leap to fatherhood: The pros and cons exercise Ben used to think through becoming a parent and what ultimately pushed him to take the leap.
• What makes a portfolio career work: How Ben structures his time across fractional work, teaching, building an AI product, and podcasting without feeling overwhelmed.
• Structure as a path to freedom: Why routines have become essential for Ben and how they help him stay present, productive, and connected to his family.
• Handling disagreements as partners: Ben reflects on navigating different parenting styles with his wife and how they’ve built a process for staying aligned.
• Creating connection through community: How a local dad group gave Ben a deeper sense of belonging and why it’s made parenting feel a little less isolating.

Where to find Ben Erez

• LinkedIn: https://www.linkedin.com/in/benerez/
• X: https://x.com/viableben

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com
• LinkedIn: https://www.linkedin.com/in/adamjfishman/
• Instagram: https://ww.instagram.com/startupdadpod/

In this episode, we cover:
(00:00) Introducing Ben Erez
(01:12) Raising a toddler and golden retriever
(04:29) Experiencing the magic of girl dad life
(08:42) Building a sustainable portfolio career
(14:56) Rethinking job security as a solopreneur
(18:35) The pros and cons of having kids
(22:36) Discovering the ease of solo parenting
(27:31) Why weekends feel less flexible now
(30:02) Feeling at home while traveling with kids
(34:28) Bedtime routines that actually work
(38:20) Handling disagreements with your partner
(42:22) How a dad group changed everything
(47:47) Navigating screen time and tech exposure
(53:08) Lightning round: morning vs. evening routines

Show references:

YouTube Kids: https://www.youtubekids.com/

iPad: https://www.apple.com/

Perplexity.ai: https://www.perplexity.ai/

Khan Academy: https://www.khanacademy.org/

Sound Machine: https://www.amazon.com/dp/B00A2JBMRE?th=1

Table top changing pad: https://www.amazon.com/dp/B08KHD615K

Unspeakable: https://www.youtube.com/channel/UCwIWAbIeu0xI0ReKWOcw3eg

Blippi: https://www.youtube.com/channel/UC5PYHgAzJ1wLEidB58SK6Xw

Moana: https://www.imdb.com/title/tt3521164/

Ghostbusters: https://www.imdb.com/title/tt0087332/

Porsche: https://www.porsche.com/usa/

—

For sponsorship inquiries email: podcast@fishmana.com.
For Startup Dad Merch: www.startupdadshop.com

Jamie Lee is the Founder of JME Labs, a consulting business supporting startups and small businesses. Her husband, Jeff Okita, is the VP of Product at Tilt, a leave management platform. Together, they’re raising their 14-month-old daughter while managing demanding careers and a shared vision of parenting. We talked about:

• Building a strong support system: How Jamie and Jeff rely on an extended team of experts, family, and tools to make daily life manageable.
• Creating structure through rituals and check-ins: The methods they use to stay coordinated, including weekly planning and monthly reviews.
• Designing life around core values: Why they prioritize individual and shared time to stay connected to who they were before becoming parents.
• Traveling with a baby across continents: What 15 flights and two international trips have taught them about adaptability and preparation.
• Reevaluating the role of work: How becoming parents led both of them to rethink what success and fulfillment mean in their careers.
• Connection as a two-way street: Jeff’s take on bonding as a non-birthing parent and the moments that helped him feel truly needed.
• Challenging traditional roles in parenting: The decisions they’ve made to balance the mental, physical, and emotional load of raising a child.
• Preparing for an AI-powered future: Their early thoughts on how to raise a child in a world shaped by fast-moving technology.

Where to find Jamie Lee

• LinkedIn: https://www.linkedin.com/in/jamieannlee/
• JME Labs: https://www.jamiealee.com/

Where to find Jeff Okita

• LinkedIn: https://www.linkedin.com/in/jeffokita/
• Tilt: https://hellotilt.com/

Where to find Adam Fishman

• FishmanAF Newsletter: www.FishmanAFNewsletter.com
• LinkedIn: https://www.linkedin.com/in/adamjfishman/
• Instagram: https://ww.instagram.com/startupdadpod/

In this episode, we cover:
(00:00) Introducing Jamie and Jeff

(02:20) What is the “extended team” in their household

(04:35) Emergency childcare plans and calendar blow-ups

(05:08) The four C’s of parenting: Coordination, Communication, Compromise, Creativity

(06:06) Running, nursing, errands, and multitasking hacks

(07:27) Rituals for communication and monthly check-ins

(08:38) Me, Me, and We Nights

(11:09) Where their parenting systems came from

(13:33) Hiring a postpartum doula and learning on the fly

(14:22) 15 flights with a baby and international travel strategies

(17:39) Potato, plant, and puppy phases of babyhood

(20:14) Blowouts on the road and travel horror stories

(24:34) Not losing yourself post-baby

(28:59) Rethinking the role of work after having a child

(34:07) Building connection with your baby and rejecting the parenting default

(54:57) Lightning Round: parenting quirks, pre-baby routines, and toddler travel wins

Resources from this episode:
ChatGPT.com

Die With Zero: Getting All You Can from Your Money and Your Life by Bill Perkins: https://bndl.co/3XlKH6e

Blank Check: https://imdb.to/3Vjc3T5

Planet Earth: https://imdb.to/3XlYoTo

—

Want to sponsor this podcast? Email podcast@fishmana.com
For Startup Dad Merch: www.startupdadshop.com

Alex Medick is the Director of Marketing at TensorWave, an AI infrastructure company. Prior to this role, he served as the President and Chief Marketing Officer of Inside.com.

He’s also a single dad to two kids, a son and a daughter, navigating the challenges of parenting while leading in the startup world.

We discussed:
- Balancing parenting with startup demands: How Alex manages being the primary parent while navigating the challenges of working at a fast-paced startup.
- Communicating with kids during a separation: The approach Alex took to talk to his young children about his separation and how it affected them.
- Unexpected fulfillment from fatherhood: How becoming a dad has brought a deeper sense of fulfillment and perspective to Alex’s life.
- Giving yourself grace as a parent: Why Alex’s motto is to give yourself grace, especially during the hectic and overwhelming times.
- The “sucky” moments that create lasting memories: Alex shares how saying yes to the challenging moments, like chaotic travel and events, leads to some of the most memorable experiences.
- Old school parenting in modern times: Alex talks about his approach to parenting, influenced by older generations, and why he believes kids need more structure and less coddling.

Where to find Alex Medick
LinkedIn: https://www.linkedin.com/in/ajmedick/
X: https://x.com/ajmedick
TensorWave: https://tensorwave.com/

Where to find Adam Fishman
FishmanAF Newsletter: www.FishmanAFNewsletter.com
LinkedIn: https://www.linkedin.com/in/adamjfishman/
Instagram: https://ww.instagram.com/startupdadpod/

In this episode, we cover:
(00:00) Introducing Alex Medick
(02:10) Balancing parenting with startup life
(03:15) Talking to kids about separation
(08:15) Unexpected fulfillment from fatherhood
(10:06) Giving yourself grace and embracing imperfection
(16:20) Old school parenting in modern times
(19:31) Hospital quarantine story and new perspective
(22:28) Travel chaos, flight disasters, and survival tips
(33:29) Raising kids with tech: balance needed
(36:03) Empathy and life principles guiding Alex
(39:50) Lightning round: must-haves and parenting quirks

Show references:
YouTube Kids: https://www.youtubekids.com/
iPad: https://www.apple.com/
Perplexity.ai: https://www.perplexity.ai/
Khan Academy: https://www.khanacademy.org/
Sound Machine: https://www.amazon.com/dp/B00A2JBMRE?th=1
Table top changing pad: https://www.amazon.com/dp/B08KHD615K

Unspeakable: https://www.youtube.com/channel/UCwIWAbIeu0xI0ReKWOcw3eg
Blippi: https://www.youtube.com/channel/UC5PYHgAzJ1wLEidB58SK6Xw
Moana: https://www.imdb.com/title/tt3521164/
Ghostbusters: https://www.imdb.com/title/tt0087332/
Porsche: https://www.porsche.com/usa/
—
For sponsorship inquiries email: podcast@fishmana.com.
For Startup Dad Merch: www.startupdadshop.com

Sol Kennedyi is the founder of BestInterest which helps co-parents navigate the messiness of that complex relationship. He is a serial founder who has built and sold multiple companies and has been the head of product at Dropcam, a PM at Google and an angel investor in companies like Coinbase, Gitlab and Instacart. In addition to being a serial entrepreneur he’s also a single, half-time dad of two kids and a co-parent. We discussed:

* Navigating divorce and co-parenting

* Important lessons he’s learned from his co-parenting role

* The adversarial system that exists in family court and treats parents like criminals

* The emotional rollercoaster of half-time parenting as a single Dad

* His experience taking an extended time off to be a full-time Dad when his daughter was young

* Mistakes he’s made as a parent that have helped him grow into the Dad he is today.

* How your kids help you heal your own relationship with your parents

* The importance of patience and slowness when raising kids

Where to find Sal Kennedy

* LinkedIn: https://www.linkedin.com/in/solkennedy/

* BestInterest App: bestinterestapp.com

* Sol’s Podcast: https://podcast.coparentingbeyondconflict.com/

Where to find Adam Fishman

* FishmanAF Newsletter: www.FishmanAFNewsletter.com

* LinkedIn: https://www.linkedin.com/in/adamjfishman/

* Instagram: https://ww.instagram.com/startupdadpod/

_

In this episode, we cover:

[1:55] Welcome

[2:11] Professional background

[3:53] Kids & divorce

[6:17] Co-parenting

[10:34] Advice for those going though this/co- parenting

[13:26] Being a half-time dad

[17:35] Strategies for setting boundaries with kids

[20:33] Decision to be a full-time dad and then back into work-force

[25:49] Does his own family use Best Interest?

[26:07] Most surprising things you’ve discovered as a dad?

[29:04] how having kids helped heal his relationship with his own parents

[32:08] Advice to younger Sol

[34:10] Transition from 1 to 2 kids

[36:48] Frameworks for parenting

[40:22] Kid’s relationship with tech

[44:48] Mistake as a dad

[49:05] Follow along

[49:59] Lightning round

[1:00:07] Thank you

—

Show references:

Coinbase: https://www.coinbase.com/

GitLab: https://about.gitlab.com/

Instacart: https://www.instacart.com/

Bug catcher: https://www.amazon.com/toys-Battat-Bungalow-Insect-Catching/dp/B01M0V474Y

Baby sock monitor (Owlet): https://owletcare.com/products/owlet-dream-sock

Pixar: https://www.pixar.com/

Star Wars: https://www.starwars.com/

Mini Cooper: https://www.miniusa.com/

—

For sponsorship inquiries email: podcast@fishmana.com.

For Startup Dad Merch: www.startupdadshop.com

Production support for Startup Dad is provided by Tommy Harron at

http://www.armaziproductions.com/